Palladium-Catalyzed Oxidative Annulation of Acrylic Acid and Amide with Alkynes: A Practical Route to Synthesize α-Pyrones and Pyridones

被引:63
|
作者
Yu, Yue [1 ]
Huang, Liangbin [1 ]
Wu, Wanqing [1 ]
Jiang, Huanfeng [1 ]
机构
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
AEROBIC INTERMOLECULAR CYCLIZATION; OXO GOLD CARBENES; C-H ACTIVATION; BENZOIC-ACIDS; GAMMA; DERIVATIVES; ALKENES; BONDS; BETA; ACETOXYPALLADATION;
D O I
10.1021/ol500611d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A range of internal alkynes smoothly underwent palladium-catalyzed oxidative annulations with acrylic acid and amide to afford alpha-pyrones and pyridones in good to excellent yields with high regioselectivity. The usage of O-2 (1 atm) as a stoichiometric oxidant with H2O as the only byproduct under mild conditions makes this process more attractive and practical.
引用
收藏
页码:2146 / 2149
页数:4
相关论文
共 50 条
  • [31] Palladium-Catalyzed Oxidative Annulation of Pyrrolylalkyl-1H-azoles: Towards the Synthesis of Polyheterocyclic Arenes
    Tripathi, Krishna N.
    Bansode, Avinash H.
    Singh, Ravi P.
    SYNTHESIS-STUTTGART, 2020, 52 (05): : 719 - 726
  • [32] Palladium-Catalyzed Synthesis of Substituted Phenanthrenes via a C-H Annulation of 2-Biaryl Triflates with Alkynes
    Prabhakaran, Mohan
    Parthasarathy, Kanniyappan
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (22) : 16363 - 16374
  • [33] Palladium-Catalyzed Annulation of Haloanilines and Halobenzamides Using Norbornadiene as an Acetylene Synthon: A Route to Functionalized Indolines, Isoquinolinones, and Indoles
    Thansandote, Praew
    Hulcoop, David G.
    Langer, Michael
    Lautens, Mark
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04) : 1673 - 1678
  • [34] Palladium-Catalyzed Sequential Nucleophilic Addition/Oxidative Annulation of Bromoalkynes with Benzoic Acids To Construct Functionalized Isocoumarins
    Jiang, Guangbin
    Li, JianXiao
    Zhu, Chuanle
    Wu, Wanqing
    Jiang, Huanfeng
    ORGANIC LETTERS, 2017, 19 (17) : 4440 - 4443
  • [35] Palladium(II)-Catalyzed Oxidative Annulation of 2-Hydroxynaphthalene-1,4-diones and Internal Alkynes via C-H Functionalization
    Sun, Peng
    Yang, Jiaojiao
    Peng, Jinsong
    Mo, Baichuan
    Chen, Xin
    Li, Xiang
    Chen, Chunxia
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (10) : 6761 - 6769
  • [36] Palladium-catalyzed oxidative annulation of N-(8-quinolinyl) aryl carboxamides with 1-aryl-2-tosyloxy ethanones
    Long, Qinghuang
    Zou, Keran
    Dong, Wanrong
    Xie, Dexun
    An, Delie
    SYNTHETIC COMMUNICATIONS, 2021, 51 (18) : 2796 - 2807
  • [37] Fused Ring Construction around Pyrrole, Indole, and Related Compounds via Palladium-Catalyzed Oxidative Coupling with Alkynes
    Yamashita, Maria
    Horiguchi, Hakaru
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) : 7481 - 7488
  • [38] Palladium-Catalyzed Carbonylative Annulation of 1-Hydroxy-o-Carborane and Internal Alkynes via Regioselective B-H Activation
    Au, Yik Ki
    Quan, Yangjian
    Xie, Zuowei
    CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (14) : 2170 - 2173
  • [39] Photoinduced Palladium-Catalyzed Regio- and Chemoselective Elimination of Primary Alkyl Bromides: A Mild Route to Synthesize Unactivated Terminal Olefins
    Yang, Sen
    Hu, Hao
    Chen, Ming
    ORGANIC LETTERS, 2023, 25 (44) : 7968 - 7973
  • [40] Palladium-Catalyzed [2+2+1] Oxidative Annulation of 4-Hydroxycoumarins with Unactivated Internal Alkynes: Access to Spiro Cyclopentadiene-Chroman-2,4-dione Complexes
    Peng, Shiyong
    Gao, Tao
    Sun, Shaofa
    Peng, Yanhong
    Wu, Minghu
    Guo, Haibing
    Wang, Jian
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (2-3) : 319 - 324